Ethyl 2-methyl-5-nitronicotinate → Ethyl 5-amino-2-methylnicotinate

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Reaction Steps

To a solution of 2-methyl-5-nitro-nicotinic acid ethyl ester 7 (1.43 mmol) in MeOH (15 mL) is added Pd (5% on carbon, 50% wet; 10% weight). After purging, the reaction mixture is stirred under hydrogen atmosphere for 3 h. The solvent is filtered through celite and the celite cake is washed with MeOH. The solvent is removed under vacuum to afford 5-amino-2-methyl-nicotinic acid ethyl ester 8 as yellow solid, which is used without further purification. 1H NMR (400 MHz, d6-DMSO) δ 7.19 (d, J=4.0 Hz, 1H), 6.78 (d, J=4.0 Hz, 2H), 4.10 (s, 2H), 3.56 (q, J=8.0 Hz, 2H), 1.80 (s, 3H), 0.59 (t, J=8.0 Hz, 3H). MS (m/z) (M+1)+: 182.0.

Provenance & Evidence